Ethylhexyl methoxycinnamates

Authors: Prof. Dr. med. Peter Altmeyer, Prof. Dr. med. Martina Bacharach-Buhles

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Last updated on: 29.10.2020

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Synonym(s)

2-ethylhexyl (2E)-3-(4-methoxyphenyl) acrylate; 2-ethylhexyl 4-methoxycinnamates; EHMC; (E,RS)-4-methoxycinnamic acid 2-ethylhexyl ester; Ethylhexylmethoxycinnamate; Octylmethoxycinnamate

Definition
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Ethylhexylmethoxycinnamate, also called octylmethoxycinnamate or EMHC for short, is an organic compound with the chemical name 2-ethylhexyl-(2E)-3-(4-methoxyphenyl)acrylate and the molecular formula: C18H26O3.

Ethylhexyl methoxycinnamate is used under the name octinoxate (ATC code D02AB02) in medical products and under the name ethylhexyl methoxycinnamate (INCI) in cosmetic products as a UV filter.

Ethylhexyl methoxycinnamate is used in products that are applied to the skin as sunscreen to absorb, reflect or scatter UV radiation (sun cream, lip care sticks).

In addition, the additive protects light-sensitive cosmetic preparations and personal care products from damage caused by UV radiation.

The use of ethylhexyl methoxycinnamate is labelled in the list of ingredients with this INCI name. In the EU, cosmetic products are subject to a maximum concentration of 10% of the pure substance in the ready-to-use preparation.

Ethylhexyl methoxycinnamate is found as "octinoxate", ATC code D02AB02, as a protective agent against UV radiation in medical preparations or drugs.

Incompatibility
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Ethylhexylmethoxycinnamate is considered to be a substance that affects the oestrogenic hormone system. When released into the environment, EMHC can be harmful to aquatic organisms with long-term effects.

Preparations
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Eusolex 2292®; Uvinul MC80®; Sunscreen AV®; Escalol®;

Note(s)
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Organic light protection filters are all those UV filters whose effect is not exclusively based on the inorganic, physically active substances titanium dioxide or zinc oxide. Organic, also known as chemical UV filters, are photoactive substances that are able to absorb light quanta in a certain wavelength range (ultraviolet radiation in the range of about 280 to 400 nm = ultraviolet radiation = UVB/UVA spectrum). The absorbed UV is then released as thermal energy without penetrating the skin. In this reversible photoisomerization, the energy of the absorbed photon must correspond to the energy required to lift an electron in the molecule of the filter substance from a lower to a higher orbit. In order to protect over the entire width of the wavelengths relevant to humans from 290 to 400 nm, several chemical filters with different absorption maxima are usually combined. With a suitable combination of organic and physical filters, the content of organic filters can also be reduced with the same UV protection. This is desirable, since especially photounstable organic UV filters can cause phototoxic and photoallergic reactions depending on their concentration in the finished product.